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Stewart was born in 1978 and raised in Los Angeles.[1] He was in several bands before Xiu Xiu, beginning in his youth. While in school, he played in a parody band and a Bauhaus cover band. After high school, he played bass in a group with guitarist Kenny Lyon and members from bands such as Devo, Geza X, The Screamers, and Sparks. Stewart has said that this experience was particularly formative for his career, but he did not realize this then. He later quit the band and moved home to attend college.[2] During this period he came out to his parents, although this was not received warmly.[3]

At home, Stewart briefly played in several other bands before being kicked out, and a high school friend suggested that he start his own band, which became IBOPA.[2][a] His father also played in the band,[4] and Stewart also played with Korea Girl during this period.[5]Metro Silicon Valley described IBOPA as a collision of "dance, lounge, disco, and ska" with the horror of Red Asphalt,[6] and noted the band for bringing attention to South Bay music.[7] IBOPA was briefly signed to an Elektra Records subsidiary in 1999, and broke up in July 1999 when the label dropped most of its artists.[8][b] The band announced that five of its members—Stewart, Cory McCulloch, Kurt Stumbaugh, Tim Kirby, and Don Dias[10]—would continue into a new acoustic and experimental band called Ten in the Swear Jar.[8]

Ten in the Swear Jar (XITSJ) continued IBOPA's "unusual approach" with eccentric and erratic music.[10][c]Metro‍ '​s David Espinoza described the band as "futuristic in instrumentation and erratic in mentality" with the traditional instrumentation backgrounded by baritone saxophones, banjos, accordions, and synthesizers.[11] He added that the band's sound was minimalistic and that the unusual instruments were not used to excess.[11] XITSJ disbanded in September 2000 and Stewart formed Xiu Xiu.[12]

Stewart started his third band, Xiu Xiu, with Cory McCullouch (from XITSJ), Yvonne Chen, and Lauren Andrews.[13] The band forgoes traditional rock instruments for programmed drums, indigenous instruments, and others including harmonium, mandolin, brass bells, gongs, keyboards, and a cross between a guitarrón mexicano and a cello for bass.[13]Metro Silicon Valley‍ '​s David Espinoza likened Stewart to an explorer charting new territories of sound in 2001 as he started Xiu Xiu.[13] He compared Stewart's voice to a combination of Robert Smith's fragility and The Downward Spiral-era Trent Reznor's anger, and noted Stewart's deliberate choice of tone in light of the individual instruments' disparate wackiness.[13] The name Xiu Xiu, pronounced "shoe shoe",[12][13] is taken from the film Xiu Xiu: The Sent Down Girl. In Stewart's description, the film's theme is that of no resolution—that awful things happen to the protagonist throughout the film and she dies at the end. The band found its first tracks to match the "rotten realness" spirit of the film, "that sometimes life turns out with a worst possible case scenario".[14] Stewart said Tracy Chapman's "Fast Car", which Xiu Xiu covered on A Promise, had a similar theme.[14]

Stewart visited Vietnam around 2001, where he took the picture that appears on the cover of A Promise. To afford the trip, he opened his equipment to local punk and ska bands as a recording studio. Stewart Stewart described the period between Knife Play and A Promise as full of "really bad things" in his personal life.[14] In 2003, Stewart said that he had been very influenced by gamelan and Korean and Japanese folk music, and that he had been listening primarily to contemporary classical and "gay dance music".[14]

Brandon Stosuy of Pitchfork said that Stewart, "one of underground music's consistently brilliant anomalies", "came into his own" on A Promise, and that his vocal style was compared with Robert Smith, Annie Lennox, and Michael McDonald.[15] He noted a "continual poetic and romantic beauty" behind "the violence" in Stewart's lyrics.[15]

The tone of 2004's Fabulous Muscles reflected an "incredibly, incredibly violent, incredibly jarring, and difficult to take" string of events in Stewart's life.[15]

When interviewing for The Air Force in 2006, Stewart said that the year was "one of the first not dominated by personal tragedies", though the tone of the album reflects his experience internalizing the events of the previous years, which he felt was "almost more difficult".[15]

Outside of music, Stewart said that he had written a "failed attempt" at a humorous novel based on "very, very peculiar sexual encounters" he had through his life.[15] He wrote for two years ending in 2005, and circulated the book to friends. Among his favorite authors, he listed Yukio Mishima, Dennis Cooper, Charles Bukowski, and Kenzaburo Oe.[15]

^IBOPA was signed to Elektra Records subsidiary Spongebath Records in April 1999 with plans to release three seven-inch records and a retrospective CD worldwide,[9] but decided to fold three months later when Spongebath dropped the majority of its talent.[8] Their last show was on July 4, 1999 at the Grand Fanali Presents Fourth of July Celebration.[8]

^Their debut album My Very Private Map was produced on CD and vinyl, and their next album, Inside the Computer Are All of My Feelings, was released on vinyl from Random Order Records.[10]